“Start your own social media site,” goes the common refrain when conservatives complain about getting kicked off Facebook and Twitter. Well, now Donald Trump has.

On Wednesday night, the former president announced the launch of the Orwellian-sounding “TRUTH Social” and “Trump Media & Technology Group.”

“I created TRUTH Social and TMTG to stand up to the tyranny of Big Tech,” Trump said in the press release. “We live in a world where the Taliban has a huge presence on Twitter, yet your favorite American President has been silenced. This is unacceptable. I am excited to send out my first TRUTH on TRUTH Social very soon.”

Interestingly, the announcement came from the Campaign Nucleus press list, an email marketing company set up by former Trump campaign manager Brad Parscale whose clients include the GOP and its fundraising platform WinRed. In his bid for tech supremacy, it seems Trump has decided to go his own way and back Parscale over other former acolytes like his 2020 senior adviser Jason Miller, who started Gettr, a social media site “founded on the principles of free speech, independent thought and rejecting political censorship and ‘cancel culture’”, earlier this year. The former president has also snubbed the Mercer-backed app Parler, whose CEO George Farmer is better known as Mr Candace Owens.

Perhaps it’s no shock that Trump’s new site immediately ran into teething problems. The Washington Post reports how “pranksters found what appeared to be an unreleased test version and posted a picture of a defecating pig to the ‘donaldjtrump’ account” and how “a Washington Post reporter was able to register and post under the account name ‘mikepence’ without any stops in place.” This is, after all, the president whose legal team delivered an “election fraud” press conference from outside a landscaping company less than a year ago. But then other social media sites aimed at conservatives have had difficulty launching too: Parler made a concerted effort to gain traction at the Conservative Political Action Conference in 2020, but hit a snag when users complained about the app’s bugginess.

That’s one of the issues with trying to rival Big Tech: the likes of Instagram and Twitter set the expectations of the market. If your product isn’t comparably functional, how can you expect to usurp the more mainstream apps?

Another problem conservative apps face is content moderation: given that Parler, Gettr and presumably TRUTH Social are presented as “free speech” alternatives to Facebook, how do they decide which posts are too far? TRUTH Social, for instance, won’t allow posts that “disparage, tarnish, or otherwise harm, in our opinion, us and/or the Site.” What kind of free speech site won’t allow its users to speak freely about it?

The flipside of the content moderation issue is liability. One of the animating impulses behind Trump launching his own site is his urge to repeal Section 230, the exemption that means social media sites can’t be held legally responsible for what users post on their platform. It’s curious then that TRUTH Social will depend on 230 to protect it in court: the site is “not responsible for…any third-party content posted on, available through, or installed from the site, including [its] content, accuracy, offensiveness, opinions [or] reliability,” according to its terms of service.

If Trump’s past business ventures tell us anything, it’s that success isn’t inevitable — and starting a successful tech company is tougher than running a golf course.